Ethanol → HCID 53909772, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([NH:28]C=O)[CH:6]=[C:7]([CH2:17][P:18]([O:24]C(C)C)([O:20]C(C)C)=[O:19])[CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2].C[Si](C)(C)Br.C(O)C.C1OC1C>ClCCl>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([NH2:28])[CH:6]=[C:7]([CH2:17][P:18]([OH:20])([OH:24])=[O:19])[CH2:8][O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:2]Participants
Procedure
0.68 g (1.49 mmol) of 5-benzyloxy-4-diisopropylphosphonomethyl-2-formylamino-pent-3-enoic acid ethyl ester is dissolved in 10 ml of dichloromethane, and 0.8 ml (6 mmol) of trimethylbromosilane is added dropwise at room temperature. The mixture is left to stand at room temperature for 6 hours, 10 ml of ethanol are added dropwise, the mixture is left to stand for a further 18 hours and is concentrated by evaporation, the residue is dissolved in 5 ml of ethanol, and a mixture of ml of propylene oxide and 5 ml of ethanol is added dropwise. A suspension forms, which is stirred at room temperature for 2 hours and is then filtered with suction. Drying yields 2-amino-5-benzyloxy-4-phosphonomethyl-pent-3-enoic acid ethyl ester having a melting point of 218°-220° (decomp.).
Workup
- waitThe mixture is left
- waitthe mixture is left
- waitto stand for a further 18 hours
- concentrationis concentrated by evaporation
- dissolutionthe residue is dissolved in 5 ml of ethanol
- additionis added dropwise
- filtrationis then filtered with suction
- customDrying
Sources & evidence
- ORD record
- ord-5f87480ab3d44977b42e92b947373191
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05488140
Reaction notes
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